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Immunochemical Determination of Caffeine and Carbamazepine in Complex Matrices Using Fluorescence Polarization

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Immunochemical Determination of Caffeine and Carbamazepine in Complex Matrices Using Fluorescence Polarization Dipl.-LMChem. Lidia Oberleitner Immunochemical Determination of Caff eine and Carbamazepine in Complex Matrices using Fluorescence Polarization BAM-Dissertationsreihe • Band 154 Berlin 2017 Die vorliegende Arbeit entstand an der Bundesanstalt für Materialforschung und -prüfung (BAM). Impressum Immunochemical Determination of Caff eine and Carbamazepine in Complex Matrices using Fluorescence Polarization 2017 Herausgeber: Bundesanstalt für Materialforschung und -prüfung (BAM) Unter den Eichen 87 12205 Berlin Telefon: +49 30 8104-0 Telefax: +49 30 8104-72222 E-Mail: [email protected] Internet: www.bam.de Copyright© 2017 by Bundesanstalt für Materialforschung und -prüfung (BAM) Layout: BAM-Referat Z.8 ISSN 1613-4249 ISBN 978-3-9818270-2-6 Immunochemical Determination of Caffeine and Carbamazepine in Complex Matrices using Fluorescence Polarization vorgelegt von Diplom-Lebensmittelchemikerin Lidia Irena Oberleitner geb. in Stuttgart von der Fakultät III – Prozesswissenschaften der Technischen Universität Berlin zur Erlangung des akademischen Grades Doktor der Naturwissenschaften -Dr. rer. nat.- genehmigte Dissertation Promotionsausschuss: Vorsitzender: Prof. Dr. Roland Lauster Gutachter: Prof. Dr. Leif-Alexander Garbe Priv.-Doz. Dr. Rudolf J. Schneider Priv.-Doz. Dr. Michael G. Weller Tag der wissenschaftlichen Aussprache: 31. März 2016 Berlin 2017 Contents Contents V Abstract IX Kurzzusammenfassung XI Abbreviations XIII 1. Introduction 1 1.1 Immunoassay 1 1.2 Fluorescence polarization immunoassay 3 1.2.1 Fluorophore tracer 4 1.2.2 Formats and instrumentation 6 1.2.3 Application to real samples 7 1.3 Antibodies 8 1.4 Caffeine in consumer products 10 1.5 Carbamazepine in the environment 12 1.5.1 Carbamazepine metabolism 12 1.5.2 Carbamazepine in wastewater treatment plants 13 1.5.3 Carbamazepine in surface waters 14 1.5.4 Analysis of carbamazepine in environmental samples 15 2. Aims of the thesis 17 3. Results and discussion 18 3.1 Fluorescence polarization immunoassays for the quantification of caffeine in beverages 18 3.1.1 Abstract 18 3.1.2 Introduction 19 3.1.3 Materials and methods 20 3.1.4 Results and discussion 23 3.1.5 Acknowledgments 29 3.2 Fluorescence polarization immunoassays for carbamazepine – Comparison of tracers and formats 30 3.2.1 Abstract 30 3.2.2 Introduction 31 V 3.2.3 Experimental 32 3.2.4 Results and discussion 35 3.2.5 Conclusions 42 3.2.6 Acknowledgements 42 3.3 Production and characterization of new monoclonal anti-carbamazepine antibodies and application to fluorescence polarization immunoassay 43 3.3.1 Abstract 43 3.3.2 Introduction 44 3.3.3 Material and methods 45 3.3.4 Results and discussion 49 3.3.5 Conclusion 61 3.3.6 Acknowledgments 62 3.4 Application of fluorescence polarization immunoassay for determination of carbamazepine in wastewater 63 3.4.1 Abstract 63 3.4.2 Introduction 63 3.4.3 Material and methods 65 3.4.4 Results and discussion 67 3.4.5 Conclusion 71 3.4.6 Acknowledgments 72 3.5 Supporting data – Automatization of FPIA on microtiter plates 73 3.5.1 Experimental 73 3.5.2 Results 73 4. Final discussion 76 4.1 Tracers for FPIA 76 4.2 Antibodies for FPIA 77 4.2.1 Improvements for the production process of monoclonal antibodies 77 4.2.2 Characteristics of the new carbamazepine specific antibody 79 4.3 Formats and instrumentation 81 4.3.1 Measurement arrangement 81 VI 4.3.2 Automatization 82 4.3.3 Evaluation 83 4.3.4 Sample throughput and measurement environment 84 4.4 Applicability of FPIA to complex matrices 85 4.4.1 Applicability of caffeine FPIA to consumer products 85 4.4.2 Applicability of carbamazepine FPIA to environmental samples 85 5. Conclusion 88 6. Bibliography 89 Publications 108 Acknowledgements 109 VII Abstract Pharmacologically active compounds are omnipresent in contemporary daily life, in our food and in our environment. The fast and easy quantification of those substances is becoming a subject of global importance. The fluorescence polarization immunoassay (FPIA) is a homogeneous mix-and-read format and a suitable tool for this purpose that offers a high sample throughput. Yet, the applicability to complex matrices can be limited by possible interaction of matrix compounds with antibodies or tracer. Caffeine is one of the most frequently consumed pharmacologically active compounds and is present in a large variety of consumer products, including beverages and cosmetics. Adverse health effects of high caffeine concentrations especially for pregnant women are under discussion. Therefore, and due to legal regulations, caffeine should be monitored. Automated FPIA measurements enabled the precise and accurate quantification of caffeine in beverages and cosmetics within 2 min. Samples could be highly diluted before analysis due to high assay sensitivity in the low µg/L range. Therefore, no matrix effects were observed. The antiepileptic drug carbamazepine (CBZ) is discussed as a marker for the elimination efficiency of wastewater treatment plants and the dispersion of their respective effluents in surface water. The development of a FPIA for CBZ included the synthesis and evaluation of different tracers. Using the optimum tracer CBZ-triglycine-5-(aminoacetamido) fluorescein, CBZ concentrations in surface waters could be measured on different platforms: one sample within 4 min in tubes or 24 samples within 20 min on microtiter plates (MTPs). For this study, a commercially available antibody was used, which led to overestimations with recovery rates up to 140% due to high cross-reactivities towards CBZ metabolites and other pharmaceuticals. For more accurate CBZ determination, a new monoclonal antibody was produced. In this attempt, methods for improving the monitoring during the production process were successfully applied, including feces screening and cell culture supernatant screening with FPIA. The new monoclonal antibody is highly specific for CBZ and showed mostly negligible cross-reactivities towards environmentally relevant compounds. Measurements at non- equilibrium state improved the sensitivity and selectivity of the developed FPIA due to slow binding kinetics of the new antibody. Additionally, this measure enables for CBZ determination over a measurement range of almost three orders of magnitude. The comprehensively characterized antibody was successfully applied for the development of sensitive homogeneous and heterogeneous immunoassays. The new antibody made the development of an on-site measurement system for the determination of CBZ in wastewater possible. After comprehensive optimization, this automated FPIA platform allows the precise quantification of CBZ in wastewater samples only pre-treated by filtration within 16 min. Recovery rates of 61 to 104% were observed. Measurements in the low µg/L range are possible without the application of tedious sample preparation techniques. Different FPIA platforms including MTPs, cuvettes and tubes were successfully applied. For the choice of the right format, the application field should be considered, e.g. desired sample throughput, usage for optimization or characterization of antibodies or if a set-up for routine measurements is sought for. For high sample throughput and optimization, FPIA performance on MTPs is advantageous. The best results for the application to real samples were obtained using kinetic FP measurements in cuvettes. IX Kurzzusammenfassung Pharmakologisch wirksame Substanzen sind weitverbreitet im täglichen Leben, unter anderem in Lebensmitteln und in der Umwelt. Die schnelle und einfache Überwachung dieser Substanzen nimmt an Bedeutung stetig zu. Für dieses Anliegen stellt der Fluoreszenz-polarisationsimmunoassay (FPIA) ein geeignetes Hilfsmittel dar und ermöglicht dabei einen hohen Probendurchsatz. Die Anwendung dieses Assays für komplexe Matrizes ist limitiert durch mögliche Wechselwirkungen von Matrixbestandteilen mit dem Antikörper oder dem Tracer. Koffein stellt eine der am häufigsten konsumierten pharmakologisch wirksamen Substanzen dar und kommt in einer Vielzahl von Konsumgütern, wie zum Beispiel in Getränken und kosmetischen Mitteln, vor. Negative gesundheitliche Effekte durch hohen Koffeinkonsum, vor allem für Schwangere, werden diskutiert. Aufgrund dessen und wegen gesetzlicher Regulierungen, sollte der Koffeingehalt verschiedener Produkte überwacht werden. Der automatisierte FPIA ermöglicht eine präzise und genaue Quantifizierung von Koffein in Getränken und kosmetischen Mitteln innerhalb von 2 min. Dank der hohen Sensitivität des Assays im niedrigen µg/L Bereich, konnten die Proben vor der Messung stark verdünnt werden, wodurch keine Matrixeffekte auftraten. Das Antiepileptikum Carbamazepin (CBZ) wird als Marker für die Reinigungsleistung von Kläranlagen und die Verteilung der Abläufe in den Oberflächengewässern diskutiert. Die Entwicklung des CBZ-FPIAs beinhaltete die Synthese und den Vergleich verschiedener Tracer. Unter Verwendung des besten Tracers, CBZ-Triglycin-5-(Aminoacetamido) Fluoreszein, konnten CBZ-Konzentrationen in Oberflächengewässern auf verschiedenen Plattformen gemessen werden: eine Probe konnte innerhalb von 4 min in Röhrchen gemessen werden, während 24 Proben auf Mikrotiterplatten (MTPs) innerhalb von 20 min vermessen wurden. Für diese Untersuchungen wurde ein kommerziell erhältlicher Antikörper verwendet. Dies führte auf Grund hoher Kreuzreaktivitäten gegenüber CBZ-Metaboliten und anderen Pharmazeutika zu Überbestimmungen mit Wiederfindungsraten von bis zu 140 %. Für eine genauere CBZ-Bestimmung wurde ein neuer monoklonaler Antikörper produziert. Dabei wurden Methoden
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